Thiocarranilide derivative



- mean nearaiaaa 'cnn'rron w. nmronn AND non ito Drawing. original applic rnrocnnnamnrzon nnnrva'rrvn.

tion filed To all it may concern:

Be it known and ROBERT L States, residing at Ak Summit and a new and he presen useful Improvemen banllide Derivatives 1s a-specificatlon.

that we, SIBLEY,

State of Ohio, '11

t in

and

understood .from the following s It is well known that aniline accelerator for the curing of rubber by sulphur, and that th tion product of aniline, i. e., thi

has greater curing advantages over t aniline as such has la its derivatives in this Para-phenylene-diamine and dimethyl-aniline as sulphide reactio valuable accelerators. ever, that'the partial troso-dimethyl-aniline base that is not para-a use.

ation filed August 12 oorarany,

CLAYTON W. Bnoronn citizens of the United ron, in the county of ave invented t in Thiocarof which the following vention relates to the art of vulcanizing caoutchouc,

will be fully pecification.

serves as an e carbon bisulphide reacocarbanilide,

ower and possesses other aniline itself, so that rgely been replaced by para-amidowell as their carbon bi- 11 products are known as We have found, howreduction of paraniby H S. produces a mido-dimethyl-aniline and which with carbon bisulphide produces thiourea which is very valuable as an accelerator.

a substituted The thiourea derivative the present in Ezmmple I.--One m s contemplatedby ventionjmay be prepared from paranitroso-dimethyl-aniline as paranitroso-dimethyl-aniline is water, or, if aqueous volat hydrogen sulphide molecular weight bu desired, in a s follows olecular wei ht of disso ved in uitable nonile solvent suchas benzol, and

lar weights is passed into and the solution at any boiling point of the solvent.

preferably equal to a t less than two molecudissolved in temperature up to the The hydrogen sulphide reacts with the paranitroso-dimethyl-aniline very sul hide.

' s ointed tion Serial No. 249,579,

this base itself constitutes 1918 accelerator.

.ticularly dire with the formati similar in composition dimethyl-aniline, this base recoverable by the the solvent and of on of a base to para-amidobeing readily simple evaporation of any excess hydrogen out in .our co-pending applicaugust. 12, a valuable The present invention is parcted, however, to

the produc- A nan/ace canton...

Em L. SIBLEY, or AKRON, time, mavens TO THE- or AKRON, omo,

A CQRPORATJION 9F OHIO.

1918, Serial No. 249,580. Divided and this applica- Krovember 24, 1919. Serial No. 340,252.

accelerator of a thiourea derivative having still more advantageous properties. This is accomplished by mixtion from this ing the sulphur-containing base in question with 'an excess of carbon bisulphide.

mixture immediately becomes hot, with the beration of hydrogen sulphide, and the resulting product is a derivative of thiourea aving very high curing power as an accelerator, and imparting a solvent, as'the solvent for the paranitrosodimethyl-aniline during its reaction with ydrogen sulphide, as above described, both of the desired reactions are carried out simultaneously. This procedure is advan: tageous in that less hydrogen sulphide need be furnished for the carrying of the reaction to the point corresponding to the product obtained in Example I, for the hydrogen sulphide produced by the carbon bisulphide reaction with the new base at once reacts with the as yet unchanged paranitroso-dimethyl-aniline to produce a further 7 quantity of the base, which, in turn, reacts with the carbon bisulphide. The reaction therefore takes a cyclic course after having been initiated, and the final reaction a carbon bisulphide solution Nil in our invention as tain as a product the carbon bisulphide reaction product of para-amido-dimethylaniline together with free sulphur.

For paranitroso-dimethyl-aniline, as given in the foregoing examples, other paramtroso bodies, such for example as paranitrosophenol maybe substituted, the amount of hydrogen sulphide and of carbon bisulphide required for reaction being of course, on a molecular basis.

The application is a division of our prior application No. 249,580, filed August 12, 1918. I

While we have set forth in considerable detail one specific manner of carrying out our invention, together with. a variant thereof, this is to be regarded as illustrative only, and for the purpose of making the invention more clear. The invention is not to be regarded as limited to the exact procedure named, nor as dependent upon the accuracy of the chemical theories which we have advanced, except in so far as such limitations are included within the terms of the accompanying claims, in which it is broadly as is pernnssible in view of the prior art.

What we claim is:

1. The thiourea derivatives constituting the product formed by the simultaneous reaction of carbon bisulphide and hydrogen sulphide on a paramtroso body.

2. The thiourea derivative constituting the product formed by the simultaneous reaction of carbon bisulphide and hydrogen sulphide on paranitroso-dimethyl-aniline.

3. The method of preparing a thiourea derivative which consists in reacting upon our intention to claim all novelty inherent.

germane a paranitroso body with carbon bisulphide and h drogen sulphide simultaneously.

4:- he method of preparing a thiourea derivative which consists in reactin upon paranitroso-dimethyl-aniline with car on bisulphide and hydrogen sulphide simultanederivative which consists in acting upon one mol of paranitroso-dimethyl-aniline with less than two mols of hydrogen sulphide and with carbon bisulphide.

6. The method of preparing a thiourea derivative which consists in acting u on one mol of paranitroso dimethylaniiinewith one mol of hydrogen sulphide and with carbon bisulphide. v

7. The method of preparing a thiourea derivative which comprises dissolving a paranitroso bod in a solvent containing an excess of car on bisulphide and passing hydrogen sulphide into the solution.

8. The method of preparing a thiourea derivative which comprises dissolving a paranitroso, body in a solvent containing an excess of carbonbisulphide and passing hydrogen into the solution, the proportion of hydrogensulphide being less than two mols for each mol of the paranitroso body 9. The method of preparing a thiourea derivative which comprises dissolving paranitroso-dimethyl-aniline in a solvent containing an excess of carbon bisulphide and passing hydrogen sulphide into. the solution, the proportion of hydrogen sulphide being less than nitroso-dimethyl-aniline.

CLAYTON W. BEDFORD. ROBERT L. STBLEY.

usly. 5. The method of preparing a thiourea two mols for each mol of the para-- 

